Jojoba has a unique wax ester oil, which is widely used in cosmetics and lubricants. After oil extraction, the de-fatted and partially de-fatted jojoba meals contain several compounds such as simmondsin and its analogues, phytic acid, trypsin and tannin.
Simmondsins and its analogues are unique components of jojoba and have been the subject of scientific studies for about 30 years. The structures of simmondsins have been elucidated and their chemical properties defined. In this document, the term “Simmondsins” (capitalised, plural) is used to indicate three analogues of simmondsin, which include simmondsin, didemethyl simmondsin and simmondsin ferulate.
An important property of simmondsin and simmondsin ferulate is their reported ability to cause a significant food intake reduction in animals. Didemethyl simmondsin is thought not to have such efficacy. Currently, the reduction of food intake induced by simmondsin and simmondsin ferulate is attributed to the stimulation of satiation, probably through the stimulation of cholecystokinin production (Cokelaere, et al., Proceedings of the Ninth International Conference on Jojoba and Its Uses and of the Third International Conference on New Industrial Crops and Products, 135-136, 1996; Flo et al. Proceedings of the Ninth International Conference on Jojoba and Its Uses and of the Third International Conference on New Industrial Crops and Products, 135-136, 1996). Simmondsin ferulate is reported to have about 67% efficacy compared to simmondsin in tests involving rats (Cokelaere, et al., 1996). The food intake reduction induced by simmondsin and simmondsin ferulate may be useful in weight control of animals. Simmondsin and simmondsin ferulate may be extracted from jojoba meal, or any other plant containing Simmondsins, and may be used for the purpose of weight control in animals and humans.
Simondsin and its analogues may be extracted with organic solvents (i.e. acetone, methanol, ethanol and ethyl acetate) from de-fatted jojoba meal and purified by chromatographic techniques such as high performance liquid chromatography (Booth et al., Life Science 15: 1115-1120, 1974; Verbiscar and Banigan, Journal of Agricultural and Food Chemistry 26: 1456-1459, 1987; Dangreau and Cokeraere, Duch Patent No. 8901639, 1994; Van. Boven at al., Journal of Agricultural and Food Chemistry 41: 1606-1607, 1993; Van Boven at al., Journal of Agricultural and Food Chemistry 41: 1118-1121, 1994; Decuypere and Cokelaere, U.S. Pat. No. 9,425,035, 1994; Van Boven et. al., Proceedings of the Ninth International Conference on Jojoba and Its Uses and of the Third International Conference on New Industrial Crops and Products, 135-136, 1996; Abbot at al., U.S. Pat. No. 9,962,530, 1999). However, the technique of high performance liquid chromatography may be too costly to be economically feasible for industrial scale production of simmondsin products.
Erhan et al. (Industrial Crops and Products 6: 147-154, 1997) prepared a concentrate of Simmondsins in a pilot scale operation using the technique of water extraction, which was followed by ultrafiltration land spray drying. The final powdery concentrate reportedly contained about 41.3% Simmonsins.
Problematically, crude extracts or concentrates of Simmondsins generated through organic solvent or water extraction of de-fatted jojoba meal may contain odour and bitter components, and may have a strong astringent and pungent taste. Without further purification, the extract of Simmondsins may therefore not be palatable.